A general synthesis of structurally diverse building blocks for preparing analogues of C-linked antifreeze glycoproteins

被引:21
作者
Eniade, A [1 ]
Murphy, AV [1 ]
Landreau, G [1 ]
Ben, RN [1 ]
机构
[1] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA
关键词
D O I
10.1021/bc0155059
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A synthetic methodology to afford unusual glycoconjugate building blocks useful for the solid-phase synthesis of C-linked antifreeze glycoprotein (AFGP) analogues is described. Such compounds are urgently required in order to elucidate the molecular mechanism by which AFGPs function. All reactions are general in nature and accommodate structural variation in the carbohydrate moiety, polypeptide backbone, and amino acid side chain.
引用
收藏
页码:817 / 823
页数:7
相关论文
共 43 条
[1]  
Ananthanarayanan VS, 1989, LIFE CHEM REPORTS, V7, P1
[2]  
Ben RN, 2001, CHEMBIOCHEM, V2, P161, DOI 10.1002/1439-7633(20010302)2:3<161::AID-CBIC161>3.3.CO
[3]  
2-6
[4]   Synthesis of a C-linked antifreeze glycoprotein (AFGP) mimic: Probes for investigating the mechanism of action [J].
Ben, RN ;
Eniade, AA ;
Hauer, L .
ORGANIC LETTERS, 1999, 1 (11) :1759-1762
[5]   CARBON-LINKED GALACTOSPHINGOLIPID ANALOGS BIND SPECIFICALLY TO HIV-1 GP120 [J].
BERTOZZI, CR ;
COOK, DG ;
KOBERTZ, WR ;
GONZALEZSCARANO, F ;
BEDNARSKI, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10639-10641
[6]   A diminished role for hydrogen bonds in antifreeze protein binding to ice [J].
Chao, HM ;
Houston, ME ;
Hodges, RS ;
Kay, CM ;
Sykes, BD ;
Loewen, MC ;
Davies, PL ;
Sonnichsen, FD .
BIOCHEMISTRY, 1997, 36 (48) :14652-14660
[7]   Antifreeze proteins [J].
Davies, PL ;
Sykes, BD .
CURRENT OPINION IN STRUCTURAL BIOLOGY, 1997, 7 (06) :828-834
[8]   STRUCTURAL STUDIES OF ANTARCTIC FISH ANTIFREEZE GLYCOPROTEINS BY ONE-DIMENSIONAL AND 2-DIMENSIONAL NMR-SPECTROSCOPY [J].
DILL, K ;
HUANG, LH ;
BEARDEN, DW ;
FEENEY, RE .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (04) :499-517
[9]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[10]   Preparation of Tn and sialyl Tn building blocks used in Fmoc solid-phase synthesis of glycopeptide fragments from HIV gp120 [J].
Elofsson, M ;
Salvador, LA ;
Kihlberg, J .
TETRAHEDRON, 1997, 53 (01) :369-390